Bowlly was born in Lourenço Marques, in the then Portuguese colony of Mozambique, to Greek and Lebanese parents[3] who met en route to Australia and moved to South Africa. Bowlly was brought up in Johannesburg. After a series of odd jobs across South Africa in his youth, including being a barber and a jockey, he gained his musical experience singing for a dance band led by Edgar Adeler on a tour of South Africa, Rhodesia, India and Indonesia during the mid-1920s. However, he fell out with Adeler and was fired from the band in Surabaya, Indonesia. After a spell with a Filipino band in Surabaya he was then employed by Jimmy Liquime in India. Bowlly worked his passage back home by busking. Just one year after his 1927 debut recording date in Berlin, where he recorded Irving Berlin's "Blue Skies" with Edgar Adeler, Bowlly arrived in London for the first time as part of Fred Elizalde's orchestra, although he nearly didn't make it after foolishly frittering away the fare money sent to him by Elizalde.

That year, "If I Had You" became one of the first popular songs by an English jazz band to become well known in America as well, and Bowlly had gone out on his own by the beginning of the 1930s. First, however, the onset of the Great Depression in 1929 resulted in Bowlly being made redundant and returning to several months of busking to survive. In the 1930s, he signed two contracts—one in May 1931 with Roy Fox, singing in his live band for the Monseigneur Restaurant in London, the other a record contract with Ray Noble's orchestra in November 1930.

During the next four years, he recorded over 500 songs. By 1933 Lew Stone had ousted Fox as bandleader, and Bowlly was singing Stone's arrangements with Stone's band. After much radio exposure and a successful British tour with Stone, Bowlly was inundated with demands for personal appearances and gigs—including undertaking a subsequent solo British tour—but continued to make the bulk of his recordings with Noble. There was considerable competition between Noble and Stone for Bowlly's time as, for much of the year, Bowlly would spend all day in the recording studio with Noble's band, rehearsing and recording, only then to spend the evening playing live at the Monseigneur with Stone's band. (Many of these Noble sides were issued in the United States by Victor, which meant that by the time Noble and Bowlly came to America, their reputation had preceded them.)

He had appeared with his own band, the Radio City Rhythm Makers, but they had split by late 1937 when his vocal problems were traced to a wart in his throat, which briefly caused him to lose his voice. With him and Marjie separated and his band dissolved, that year he was once again down on his luck. He was forced to borrow money from friends for a trip to New York for the surgery of which he was so in need. In 1938, he finally returned to the United States to undergo successful major throat surgery for the removal of his vocal wart, but still had difficulties later in his career.

His absence from the UK in the early 1930s damaged his popularity with British audiences, despite his association with the gifted pianist, Monia Liter, as his accompanist. His career began to suffer as a result of problems with his voice from around 1936, which affected the frequency of his recordings. He played a few small parts in films around this time, yet never professed to be an actor. The parts he did play were often cut, and scenes that were shown were brief. Noble was offered a role in Hollywood although the offer did not, unfortunately, include Bowlly, as a singer had already been instated. Bowlly moved back to London with his wife Marjie in January 1937.

With his diminished success in Britain, he toured regional theatres and recorded as often as possible to make a living, moving from orchestra to orchestra, including those of Sydney Lipton, Geraldo and Ken Johnson. He underwent a revival from 1940, as part of a double act with Jimmy Messene (whose career had also suffered a recent downturn), with an act called Radio Stars with Two Guitars, performing on the London stage. It was his last venture before his death in April 1941.

The partnership was an uneasy one, as Messene suffered from a serious drinking problem by this stage, and was known to turn up incapable on stage, or to not turn up at all, much to Bowlly's consternation. His last recorded song, made two weeks before his death, was a duet with Messene of Irving Berlin's satirical song on Hitler, "When That Man is Dead and Gone".

In December 1931, Bowlly married Constance Freda Roberts in St Martin's District, London, but Bowlly discovered his new wife in bed with another man on their wedding night. The couple separated after a fortnight, and sought a rapid divorce. He remarried in December 1934, this time to Marjie Fairless, the marriage lasting until his death (Freda remarried in 1965, dying in Richmond-upon-Thames in 1967).

On 17 April 1941, Bowlly and Messene had just given a performance at the Rex Cinema in Oxford Street, High Wycombe, now demolished. Both were offered the opportunity of an overnight stay in the town, but Bowlly opted to take the last train home to his flat at 32 Duke Street, Duke's Court, St James, London. His decision proved to be fatal, as he was killed by a Luftwaffeparachute mine that detonated outside his flat later that evening.[4] His body appeared unmarked: although the massive explosion had not disfigured him, it had blown his bedroom door off its hinges and the impact against his head proved fatal. He was buried with other bombing victims in a mass grave at what is today known as Hanwell Cemetery, Uxbridge Road, Hanwell, where his name is given as Albert Alex Bowlly.

Al Bowlly is sometimes credited with inventing crooning, or "The Modern Singing Style", releasing a book of the same name. Bowlly experimented with new methods of amplification, not least with his Melody Maker advert, showing him endorsing a portable vocal megaphone. With the advent of the microphone in 1931, Al adapted his singing style, moving away from the Jazz singing style of the 20s, into the softer, more expressive crooning singing style used in popular music of the 1930s and 1940s. It was Bowlly's technique, sincerity, diction and his personality that distinguish him from many other singers of the 1930s era.

Al is also credited[by whom?] with being the first "pop star". Prior to the advent of Bowlly, the bandleaders were the stars and the main attractions, with the records being sold as "Ray Noble and his orchestra (with vocal refrain)", a phenomenon that can be seen on 78s of the period. Most singers were all but anonymous; however, Al's popularity changed this, with him being the first singer to be given a solo spot on BBC radio due to popular demand, and records appearing featuring his own name. Bowlly's personality, good looks, charisma, and above all his voice, earned him the nickname "The Big Swoon", with Al finding himself being mobbed by female fans for autographs and photos after his performances.

As well as singing, Bowlly played both the guitar and the ukulele, with Joyce Stone, Lew Stone's wife, saying: "You only had to play anything once to Al and he'd got it." Bowlly remains one of the most highly regarded singers of his era because of his extraordinary range, his command of pitch and rhythm, and, above all, the sincerity with which he could deliver a lyric. Ray Noble is often quoted as saying that Al often stepped away from the microphone with tears in his eyes; "never mind him making you cry, he could make himself cry!"

In 1978, "Isn't It Heavenly" by Lew Stone and his Band featuring Al Bowlly was used in the award-winning television series Edward and Mrs Simpson made by Thames Television, starring Edward Fox and Cynthia Harris in the lead roles. The couple are seen dancing in their Hotel suite c. 1935. It is a touching moment as they romantically live Al Bowlly's song message. There were two recordings of this song for Decca Records on 1 August 1933 and 25 October 1933 respectively, listing Lew Stone and the Monseigneur Band. It is not known which recording was selected for the television series.

In 1986, British singer/songwriter/guitarist Richard Thompson paid tribute on his album Daring Adventures with the song "Al Bowlly's in Heaven", about a veteran who reminisces about the days when he used to see Bowlly sing in the clubs of London.

In 1990, Bowlly's recording of "The Very Thought of You" was used in Australia for the advertising campaign for Dine Cat Food.

"Midnight, the Stars and You" has been used for many years as the final closing music for Nightline with Bruce Mansfield and Philip Brady on radio 3AW, in Melbourne, Australia.

"Midnight, the Stars and You" has been the signature piece and the final music cut since 2001 on the John Batchelor Show, an American national radio program.

According to her appearance on the radio show Wits, Sadie Doyle (one of the leads from Beyond Belief, part of The Thrilling Adventure Hour, played by Paget Brewster), "Midnight, the Stars and You" was her first favorite song, but (in her words) "it's not canonical".

John Lawton's book "Riptide" (published as "Bluffing Mr Churchill" in the US) takes its name from one of Bowlly's songs and references his popularity and death in the novel.

"My Hat's on the Side of My Head" was prominently featured in the movie Murphy's War (1971)